GB2575261B - Intermediates in the synthesis of C3-substituted cephalosporins - Google Patents

Intermediates in the synthesis of C3-substituted cephalosporins Download PDF

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Publication number
GB2575261B
GB2575261B GB1810849.8A GB201810849A GB2575261B GB 2575261 B GB2575261 B GB 2575261B GB 201810849 A GB201810849 A GB 201810849A GB 2575261 B GB2575261 B GB 2575261B
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GB
United Kingdom
Prior art keywords
intermediates
synthesis
substituted cephalosporins
cephalosporins
substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
GB1810849.8A
Other versions
GB2575261A (en
GB201810849D0 (en
Inventor
Madela Karolina
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Norbrook Laboratories Ltd
Original Assignee
Norbrook Laboratories Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Norbrook Laboratories Ltd filed Critical Norbrook Laboratories Ltd
Priority to GB1810849.8A priority Critical patent/GB2575261B/en
Publication of GB201810849D0 publication Critical patent/GB201810849D0/en
Priority to PCT/GB2019/051871 priority patent/WO2020008183A1/en
Priority to CA3104110A priority patent/CA3104110A1/en
Priority to US17/255,371 priority patent/US11840544B2/en
Priority to AU2019298749A priority patent/AU2019298749B2/en
Priority to EP19736478.9A priority patent/EP3818059A1/en
Publication of GB2575261A publication Critical patent/GB2575261A/en
Application granted granted Critical
Publication of GB2575261B publication Critical patent/GB2575261B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D463/00—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D463/10—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • C07D463/14—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hetero atoms directly attached in position 7
    • C07D463/16—Nitrogen atoms
    • C07D463/18—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof
    • C07D463/20—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof with the acylating radicals further substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D463/22—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof with the acylating radicals further substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen further substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/02—Preparation
    • C07D501/08—Preparation by forming the ring or condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/02—Preparation
    • C07D501/08—Preparation by forming the ring or condensed ring systems
    • C07D501/10—Preparation by forming the ring or condensed ring systems from compounds containing the penicillin ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
GB1810849.8A 2018-07-02 2018-07-02 Intermediates in the synthesis of C3-substituted cephalosporins Active GB2575261B (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB1810849.8A GB2575261B (en) 2018-07-02 2018-07-02 Intermediates in the synthesis of C3-substituted cephalosporins
AU2019298749A AU2019298749B2 (en) 2018-07-02 2019-07-02 Intermediates in the synthesis of C3-substituted cephalosporins
CA3104110A CA3104110A1 (en) 2018-07-02 2019-07-02 Intermediates in the synthesis of c3-substituted cephalosporins
US17/255,371 US11840544B2 (en) 2018-07-02 2019-07-02 Intermediates in the synthesis of C3-substituted cephalosporins
PCT/GB2019/051871 WO2020008183A1 (en) 2018-07-02 2019-07-02 Intermediates in the synthesis of c3-substituted cephalosporins
EP19736478.9A EP3818059A1 (en) 2018-07-02 2019-07-02 Intermediates in the synthesis of c3-substituted cephalosporins

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1810849.8A GB2575261B (en) 2018-07-02 2018-07-02 Intermediates in the synthesis of C3-substituted cephalosporins

Publications (3)

Publication Number Publication Date
GB201810849D0 GB201810849D0 (en) 2018-08-15
GB2575261A GB2575261A (en) 2020-01-08
GB2575261B true GB2575261B (en) 2022-03-09

Family

ID=63143782

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1810849.8A Active GB2575261B (en) 2018-07-02 2018-07-02 Intermediates in the synthesis of C3-substituted cephalosporins

Country Status (6)

Country Link
US (1) US11840544B2 (en)
EP (1) EP3818059A1 (en)
AU (1) AU2019298749B2 (en)
CA (1) CA3104110A1 (en)
GB (1) GB2575261B (en)
WO (1) WO2020008183A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111892612A (en) * 2020-07-31 2020-11-06 重庆医药高等专科学校 Intermediate isomeride for preparing cefuroxime from penicillin sylvite and preparation method thereof
CN111763221A (en) * 2020-07-31 2020-10-13 重庆医药高等专科学校 Cefavistin intermediate and preparation method thereof
CN112409382A (en) * 2020-11-26 2021-02-26 浙江普洛得邦制药有限公司 Synthesis method of cefetamet pivoxil hydrochloride

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4518528A (en) * 1983-05-19 1985-05-21 Rasnick David W α Amino fluoro ketones
WO2010117796A2 (en) * 2009-03-30 2010-10-14 Codexis, Inc. Processes for the preparation of alpha-chloroketones from carboxylic acids

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MY106399A (en) 1990-07-24 1995-05-30 Pfizer Cephalosporins and homologeus, preparation and pharmaceutical composition
GB2300856A (en) 1995-05-16 1996-11-20 Pfizer Ltd Beta-lactam preparation
GB0019124D0 (en) 2000-08-03 2000-09-27 Pfizer Novel process
JP2004520293A (en) 2000-12-04 2004-07-08 ファイザー・プロダクツ・インク Coupling methods and intermediates useful for preparing cephalosporins
CN1243756C (en) 2000-12-04 2006-03-01 辉瑞产品公司 Process and ester derivatives for preparing cephalosporins
US7378408B2 (en) 2001-11-30 2008-05-27 Pfizer Inc. Methods of treatment and formulations of cephalosporin
BRPI0508595A (en) 2004-03-09 2007-08-21 Pfizer Prod Inc Process for preparing cephalosporin intermediates using alpha-iodo-1-azetidine acetic acid esters and trialkyl phosphites
US7560575B2 (en) 2005-12-28 2009-07-14 Acino Pharma Ag Process for preparation of racemic Nebivolol

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4518528A (en) * 1983-05-19 1985-05-21 Rasnick David W α Amino fluoro ketones
WO2010117796A2 (en) * 2009-03-30 2010-10-14 Codexis, Inc. Processes for the preparation of alpha-chloroketones from carboxylic acids

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Journal of Medicinal Chemistry, Vol. 57, 2014, F W GOLDBERG, "Optimiszation of brain penetrant 11-beta-hydroxysteroid dehydrogenase type I inhibitors and in vivo testing in diet-induced obese mice", pages 970-986 *

Also Published As

Publication number Publication date
WO2020008183A1 (en) 2020-01-09
US11840544B2 (en) 2023-12-12
AU2019298749A1 (en) 2021-01-28
GB2575261A (en) 2020-01-08
AU2019298749B2 (en) 2024-04-11
EP3818059A1 (en) 2021-05-12
CA3104110A1 (en) 2020-01-09
US20210261571A1 (en) 2021-08-26
GB201810849D0 (en) 2018-08-15

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